Are there any real world situations where a fixed length scenario is more analogous than a random length one?
Most of them. Dating, a night out at the bar, employment, driving somewhere, etc, etc. If you take a Gods-eye view and mash these all together, sure, our life is one big indefinite-length IPD, but at that point you've lost so much information that it's not clear that chunks of a good indefinite strategy map to good definite strategies.
LOL @ dating being analogous to a fixed length iterated Prisoner's Dilemma. [insert tired cliché joke about nerds here]
Last year, there was a lot of interest in the IPD tournament with people asking for regular events of this sort and developing new strategies (like Afterparty) within hours after the results were published and also expressing interest in re-running the tournament with new rules that allowed for submitted strategies to evolve or read their opponent's source code. I noticed that many of the submitted strategies performed poorly because of a lack of understanding of the underlying mechanics, so I wrote a comprehensive article on IPD math that sparked some interesting comments.
And then the whole thing was never spoken of again.
So now I'd like to know: How many LWers would commit to competing in another tournament of this kind, and would someone be interested in hosting it?